Sameuramide A, a new cyclic depsipeptide isolated from an ascidian of the family Didemnidae

Koshi Machida; Daisuke Arai; Ryosuke Katsumata; Satoshi Otsuka; Jun K Yamashita; Tao Ye; Shoubin Tang; Nobuhiro Fusetani; Yoichi Nakao

doi:10.1016/j.bmc.2018.06.042

Sameuramide A, a new cyclic depsipeptide isolated from an ascidian of the family Didemnidae

Bioorg Med Chem. 2018 Jul 30;26(13):3852-3857. doi: 10.1016/j.bmc.2018.06.042. Epub 2018 Jun 30.

Authors

Koshi Machida¹, Daisuke Arai², Ryosuke Katsumata³, Satoshi Otsuka³, Jun K Yamashita⁴, Tao Ye⁵, Shoubin Tang⁵, Nobuhiro Fusetani⁶, Yoichi Nakao⁷

Affiliations

¹ Department of Chemistry and Biochemistry, Graduate School of Advanced Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan; Research Institute for Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan.
² Research Institute for Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan.
³ Department of Chemistry and Biochemistry, Graduate School of Advanced Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan.
⁴ Department of Cell Growth and Differentiation, Center for iPS Cell Research and Application, Kyoto University, 53 Shogoin Kawahara-cho, Sakyo-ku, Kyoto 606-8507, Japan.
⁵ State Key Laboratory of Chemical Oncogenomics, Peking University Shenzhen Graduate School, Xili, Nanshan District, Shenzhen 518055, China.
⁶ Fisheries and Oceans Hakodate, 3-1-1 Minato-cho, Hakodate 041-8611, Japan.
⁷ Department of Chemistry and Biochemistry, Graduate School of Advanced Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan; Research Institute for Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan. Electronic address: ayocha@waseda.jp.

PMID: 29983284
DOI: 10.1016/j.bmc.2018.06.042

Abstract

Sameuramide A (1), a new cyclic depsipeptide encompassing one each of alanine, N-methyl alanine, N-methyl dehydroalanine, N,O-dimethyl threonine, phenyllactic acid, three β-hydroxy leucines, and two propionates, was isolated from a didemnid ascidian collected at the northern part of Japan. The planar structure was established based on the interpretation of MS and NMR data. The absolute configuration of the subunits was determined by the advanced Marfey's method and the chiral LC-MS analysis. Compound 1 exhibited the activity of maintaining colony formation of murine embryonic stem (mES) cells without leukemia inhibitory factor (LIF). Down regulation of the gene expression of Krüppel-like transcription factor 4 (Klf4) indicated that 1 itself was not able to maintain the undifferentiated state of the mES cells. However, the expression levels of the marker genes (Nestin, T, Sox17) for three germ layers were upregulated in embryoid bodies (EBs) after treatment of 1 together with LIF, suggesting that 1 plays a supportive role for LIF in maintaining the multipotency of mES cells.

Keywords: Colony formation; Didemnid ascidian; Embryonic stem cells; Marine natural products; Peptide.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Cell Differentiation / drug effects
Chromatography, High Pressure Liquid
Depsipeptides / chemistry*
Depsipeptides / isolation & purification
Depsipeptides / pharmacology
Down-Regulation / drug effects
Embryoid Bodies / cytology
Embryoid Bodies / drug effects
Embryoid Bodies / metabolism
Embryonic Stem Cells
HMGB Proteins / metabolism
Kruppel-Like Factor 4
Kruppel-Like Transcription Factors / metabolism
Magnetic Resonance Spectroscopy
Mass Spectrometry
Mice
Molecular Conformation
SOXF Transcription Factors / metabolism
Up-Regulation / drug effects
Urochordata / chemistry*
Urochordata / metabolism

Substances

Depsipeptides
HMGB Proteins
Klf4 protein, mouse
Kruppel-Like Factor 4
Kruppel-Like Transcription Factors
SOXF Transcription Factors
Sox17 protein, mouse
sameuramide A